Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase

Heteroaryl 1-thio-β-D-galactofuranosides have been synthesized and evaluated as inhibitors of the exo-β-D-galactofuranosidase from Penicillium fellutanum. 2-Pyridinethiol, 4-pyridinethiol, 1-methylimidazole-2-thiol, 5-methy1-1,3,4-thiadiazole-2-thiol, 2-pyrimidinethiol and 4,6-dimethyl-2- pyrimidine...

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Detalles Bibliográficos
Autores principales:	Mariño, K., Marino, C.
Formato:	JOUR
Materias:	Galactofuranose Galactofuranosidase inhibitors Glycobiology Heteroaryl 1-thio-β-D-galactofuranosides
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p341_Marino
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

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spelling	todo:paper_14246376_v2005_n12_p341_Marino2023-10-03T16:13:43Z Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase Mariño, K. Marino, C. Galactofuranose Galactofuranosidase inhibitors Glycobiology Heteroaryl 1-thio-β-D-galactofuranosides Heteroaryl 1-thio-β-D-galactofuranosides have been synthesized and evaluated as inhibitors of the exo-β-D-galactofuranosidase from Penicillium fellutanum. 2-Pyridinethiol, 4-pyridinethiol, 1-methylimidazole-2-thiol, 5-methy1-1,3,4-thiadiazole-2-thiol, 2-pyrimidinethiol and 4,6-dimethyl-2- pyrimidinethiol were employed as thiols, as such heteroaromatic aglycons are expected to display particular interactions with the active site of the enzyme. These thiols were condensed with per-O-benzoyl-D-galactofuranose, in the presence of SnCl4 or BF3.OEt2, followed by O-debenzoylation under mild conditions to afford the heteroaryl 1-thio-β-D-galactofuranosides in high yields. The enzymatic assays showed that 4,6-dimethyl-2-pyrimidyl 1-thio-β-D-galactofuranoside was the best inhibitor (IC50 135 μM), considerable more potent than the analogue lacking the methyl groups in the aglycon moiety. © ARKAT USA, Inc. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p341_Marino
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Galactofuranose Galactofuranosidase inhibitors Glycobiology Heteroaryl 1-thio-β-D-galactofuranosides
spellingShingle	Galactofuranose Galactofuranosidase inhibitors Glycobiology Heteroaryl 1-thio-β-D-galactofuranosides Mariño, K. Marino, C. Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase
topic_facet	Galactofuranose Galactofuranosidase inhibitors Glycobiology Heteroaryl 1-thio-β-D-galactofuranosides
description	Heteroaryl 1-thio-β-D-galactofuranosides have been synthesized and evaluated as inhibitors of the exo-β-D-galactofuranosidase from Penicillium fellutanum. 2-Pyridinethiol, 4-pyridinethiol, 1-methylimidazole-2-thiol, 5-methy1-1,3,4-thiadiazole-2-thiol, 2-pyrimidinethiol and 4,6-dimethyl-2- pyrimidinethiol were employed as thiols, as such heteroaromatic aglycons are expected to display particular interactions with the active site of the enzyme. These thiols were condensed with per-O-benzoyl-D-galactofuranose, in the presence of SnCl4 or BF3.OEt2, followed by O-debenzoylation under mild conditions to afford the heteroaryl 1-thio-β-D-galactofuranosides in high yields. The enzymatic assays showed that 4,6-dimethyl-2-pyrimidyl 1-thio-β-D-galactofuranoside was the best inhibitor (IC50 135 μM), considerable more potent than the analogue lacking the methyl groups in the aglycon moiety. © ARKAT USA, Inc.
format	JOUR
author	Mariño, K. Marino, C.
author_facet	Mariño, K. Marino, C.
author_sort	Mariño, K.
title	Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase
title_short	Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase
title_full	Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase
title_fullStr	Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase
title_full_unstemmed	Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase
title_sort	synthesis of heteroaryl 1-thio-β-d-galactofuranosides and evaluation of their inhibitory activity towards a β-d-galactofuranosidase
url	http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p341_Marino
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Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase

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